Efficient and simple methods for the introduction of the sulfonyl, acyl and alkyl protecting groups on the nitrogen of indole and its derivatives

Ottoni, Olı́via; Cruz, Rosimeire P. A.; Alves, Robledo

doi:10.1016/s0040-4020(98)00865-5

Cited by 94 publications

(59 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Then, acetic anhydride and nitromethane (co-solvent) were added to give, after work-up, 3-acetylindoles 7 (51-78%). In step b, depending upon alkylating reagents, two experimental conditions were used for the N-alkylation [29]: a phase transfer process and dimethylsulfate led to N-methylated compounds 5c, 5e, 5g and 5h (72-91%); addition of alkylhalides into mixtures of potassium hydroxide and indoles in polar solvents (ethanol, acetone or DMF) to give N-alkylated compounds 8 to 11 (58-96%). Compounds 5d, 5f and 5k were by-products of the enaminones syntheses 4 (see part 1).…”

Section: Resultsmentioning

confidence: 99%

Towards the Syntheses of N—H and N‐Alkylated Derivatives of Meridianins.

Simon¹,

Couthon‐Gourvès²,

Haelters³

et al. 2007

ChemInform

View full text Add to dashboard Cite

show abstract

Section: Resultsmentioning

confidence: 99%

Towards the Syntheses of N—H and N‐Alkylated Derivatives of Meridianins.

Simon¹,

Couthon‐Gourvès²,

Haelters³

et al. 2007

ChemInform

View full text Add to dashboard Cite

show abstract

“…The organic phase was dried (Na 2 SO 4 ), evaporated under reduced pressure and purified by column chromatography using DCM as eluent. Yield 90%; analytical and spectroscopic data were previously reported [33]. …”

Section: Methodsmentioning

confidence: 99%

Synthesis and Antitumor Activity of New Thiazole Nortopsentin Analogs

Spanò¹,

Attanzio²,

Cascioferro³

et al. 2016

Marine Drugs

View full text Add to dashboard Cite

New thiazole nortopsentin analogs in which one of the two indole units was replaced by a naphthyl and/or 7-azaindolyl portion, were conveniently synthesized. Among these, three derivatives showed good antiproliferative activity, in particular against MCF7 cell line, with GI50 values in the micromolar range. Their cytotoxic effect on MCF7 cells was further investigated in order to elucidate their mode of action. Results showed that the three compounds act as pro-apoptotic agents inducing a clear shift of viable cells towards early apoptosis, while not exerting necrotic effects. They also caused cell cycle perturbation with significant decrease in the percentage of cells in the G0/G1 and S phases, accompanied by a concomitant percentage increase of cells in the G2/M phase, and appearance of a subG1-cell population.

show abstract

“…A simple and convenient route for the synthesis of 5'-(substituted)-2',4'-dihydrospiro (indoline-3,3'-pyrazol)-2-ones and quinoline-4-carboxylic acids was summed up in Figure 1. Different aryl methyl ketones, namely 1-(6-substituted-4-methoxybenzofuran-5-yl)-ethan-1-ones 2a-c [19][20][21], 1-(6-substituted-4,7-dimethoxybenzofuran-5-yl)-ethan-1-ones 3a-c [19][20][21] and N-substituted-3-indolyl methyl ketones 4a-i [22,23], were prepared as starting materials for this study. Aldol condensation of isatin (1) with each aryl methyl ketones 2a-c, 3a-c and 4a-i in the presence of a catalytic amount of diethylamine under stirring for approximately 10-15 days at room temperature yielded the resultant aldol products: 3-hydroxy-3-(2-(aryl)-2-oxoethyl) indolin-2-ones 5a-c, 6a-c and 7a-i.…”

Section: Chemistrymentioning

confidence: 99%

“…Volume containing 50 mg of total protein was incubated with 5 mL of caspase substrate in 100 mL of the reaction buffer at 37 • C for 1 h in the dark. Caspase-3 activity was determined by a microplate reader at 405 nm using a caspase-3 colorimetric assay kit (Abcam) according to the manufacturer's instructions [23]. In vitro protein level quantitative measurement of apoptotic marker p53, Bcl-2-associated X (Bax) and antiapoptotic marker B-cell lymphoma-2 (Bcl-2) in cell lysate were assessed by Enzyme-Linked Immunosorbent Assay Simple Step ELISA ® (ab199080, ab119506 and ab171571; Abcam) according to the manufacturer's instructions [35][36][37].…”

Section: Apoptosis Assaymentioning

confidence: 99%

Synthesis and Bioactivity Assessment of Novel Spiro Pyrazole-Oxindole Congeners Exhibiting Potent and Selective in vitro Anticancer Effects

et al. 2020

View full text Add to dashboard Cite

The present work aims to design and synthesize novel series of spiro pyrazole-3,3'-oxindoles analogues and investigate their bioactivity as antioxidant and antimicrobial agents, as well as antiproliferative potency against selected human cancerous cell lines (i.e., breast, MCF-7; colon, HCT-116 and liver, HepG-2) relative to healthy noncancerous control skin fibroblast cells (BJ-1). The mechanism of their cytotoxic activity has been also examined by immunoassaying the levels of key anti-and proapoptotic protein markers. The analytical and spectral data of the all synthesized target congeners were compatible with their structures. Synthesized compounds showed diverse moderate to powerful antimicrobial and antioxidant activities. Results of MTT assay revealed that seven synthesized compounds (i.e., 11a, 11b, 12a, 12b, 13b, 13c and 13h) particularly exhibited significant cytotoxicity against the three cancerous cell lines under investigation. Ranges of IC 50 values obtained were 5.7-21.3 and 5.8-37.4 µg/mL against HCT-116 and MCF-7, respectively; which is 3.8 and 6.5-fold (based on the least IC 50 values) more significant relative to the reference chemotherapeutic drug doxorubicin. In HepG-2 cells, the analogue 13h exhibited the highest cytotoxicity with IC 50 value of 19.2µg/mL relative to doxorubicin (IC 50 = 21.6µg/mL). The observed cytotoxicity was specific to cancerous cells, as evidenced by the minimal toxicity in the noncancerous control skin-fibroblast cells. ELISA results indicated that the observed antiproliferative effect against examined cancer cell lines is mediated via engaging the activation of apoptosis as illustrated by the significant increase in proapoptotic protein markers (p53, bax and caspase-3) and reduction in the antiapoptotic marker bcl-2. Taken together, results of the present study emphasize the potential of spiro pyrazole-oxindole analogues as valuable candidate anticancer agents against human cancer cells.

show abstract

Efficient and simple methods for the introduction of the sulfonyl, acyl and alkyl protecting groups on the nitrogen of indole and its derivatives

Cited by 94 publications

References 28 publications

Towards the Syntheses of N—H and N‐Alkylated Derivatives of Meridianins.

Towards the Syntheses of N—H and N‐Alkylated Derivatives of Meridianins.

Synthesis and Antitumor Activity of New Thiazole Nortopsentin Analogs

Synthesis and Bioactivity Assessment of Novel Spiro Pyrazole-Oxindole Congeners Exhibiting Potent and Selective in vitro Anticancer Effects

Contact Info

Product

Resources

About